Oxathiinecarboxamides

ABSTRACT

This invention relates to novel oxathiinecarboxamides of the formula (I) 
     
       
         
         
             
             
         
       
         
         
           
             in which R, R 1  and m are as defined in the disclosure, to a plurality of processes for preparing these substances and to their use for controlling unwanted micro-organisms.

The present patent application has been filed under 35 U.S.C. 371 as anational stage application of PCT/EP03/05103, filed May 15, 2003, whichwas published in German as International Patent Publication WO 03/099804on Dec. 4, 2003, which is entitled to the right of priority of GermanPatent Application 102 22 886.8, filed May 23, 2002.

The present invention relates to novel oxathiinecarboxamides, to aplurality of processes for their preparation and to their use forcontrolling unwanted micro-organisms.

It is already known that numerous carboxanilides have fungicidalproperties (compare, for example, EP-A 0 545 099, EP-A 0 591 699, DE-A16 17 921, JP-A 2001-302605 and JP-A 8-176112). Thus, theoxathiinecarboxamidesN-(4′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxamide,N-(3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxamide,N-(2′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxamide,N-(3′-chloro-1,1′-biphenyl-2-yl)-2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxamideandN-(3′-methyl-1,1′-biphenyl-2-yl)-2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxamideare already known from EP-A 0 545 099. The activity of these substancesis good; however, in some cases, for example at low application rates,it is unsatisfactory.

This invention now provides novel oxathiinecarboxamides of the formula(I)

in which

-   -   R¹ represents fluorine,    -   m represents 0, 1 or 2,    -   R represents one of the groupings below,

-   -   R² represents chlorine, bromine, iodine, cyano, nitro,        C₁–C₈-alkyl, C₁–C₈-alkoxy, C₁–C₈-alkylthio, C₁–C₆-haloalkyl,        C₁–C₆-haloalkoxy or C₁–C₆-haloalkylthio having in each case from        1 to 13 fluorine, chlorine and/or bromine atoms,    -   R³ and R⁴ independently of one another represent fluorine,        chlorine, bromine, iodine, cyano, nitro, C₁–C₈-alkyl,        C₁–C₈-alkoxy, C₁–C₈-alkylthio, C₁–C₆-haloalkyl, C₁–C₆-haloalkoxy        or C₁–C₆-haloalkylthio having in each case 1 to 13 fluorine,        chlorine and/or bromine atoms,    -   n represents 3, 4 or 5 and    -   R⁵ represents identical or different radicals from the group        consisting of fluorine, chlorine, bromine, iodine, cyano, nitro,        C₁–C₈-alkyl, C₁–C₈-alkoxy, C₁–C₈-alkylthio, C₁–C₆-haloalkyl,        C₁–C₆-haloalkoxy or C₁–C₆-haloalkylthio having in each case 1 to        13 fluorine, chlorine and/or bromine atoms.

Furthermore, it has been found that oxathiinecarboxamides of the formula(I) are obtained when

-   a) carboxylic acid derivatives of the formula (II)

-   -   in which    -   G halogen, hydroxyl or C₁–C₆-alkoxy,    -   are reacted with aniline derivatives of the formula (III)

-   -   in which    -   R, R¹ and m are as defined above,    -   if appropriate in the presence of a catalyst, if appropriate in        the presence of an acid binder and if appropriate in the        presence of a diluent, or

-   b) carboxamide derivatives of the formula (IV)

-   -   in which    -   R¹ and m are as defined above,    -   are reacted with boronic acid derivatives of the formula (V)

-   -   in which    -   R is as defined above and    -   G¹ and G² each represent hydrogen or together represent        tetramethylethylene,    -   in the presence of a catalyst, if appropriate in the presence of        an acid binder and if appropriate in the presence of a diluent,        or

-   c) carboxamide boronic acid derivatives of the formula (VI)

-   -   in which    -   R¹ and m are as defined above and    -   G¹ and G² each represent hydrogen or together represent        tetramethylethylene,    -   are reacted with phenyl derivatives of the formula (VII)

-   -   in which    -   R is as defined above    -   in the presence of a catalyst, if appropriate in the presence of        a an acid binder and if appropriate in the presence of a        diluent, or

-   d) carboxamide derivatives of the formula (IV)

-   -   in which    -   R¹ and m are as defined above,    -   are reacted with phenyl derivatives of the formula (VII)

-   -   in which    -   R is as defined above,        in the presence of a palladium or platinum catalyst and in the        presence of        4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, if        appropriate in the presence of an acid binder and if appropriate        in the presence of a diluent.

Finally, it has been found that the novel oxathiinecarboxamides of theformula (I) have very good microbicidal properties and can be used forcontrolling unwanted micro-organisms both in crop protection and in theprotection of materials.

Surprisingly, the oxathiinecarboxamides of the formula (I) according tothe invention have considerably better fungicidal activity than theconstitutionally most similar active compounds of the prior art havingthe same direction of action.

The formula (I) provides a general definition of theoxathiinecarboxamides of the invention.

Preference is given to oxathiinecarboxamides of the formula (I), inwhich

-   R¹ represents fluorine,-   m represents 0, 1 or 2,-   R represents one of the groupings below,

-   R² represents chlorine, bromine, C₁–C₆-alkyl, C₁–C₆-alkoxy,    C₁–C₆-alkylthio, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy,    C₁–C₄-haloalkylthio having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms,-   R² furthermore represents cyano,-   R³ and R⁴ independently of one another represent fluorine, chlorine,    bromine, C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₆-alkylthio,    C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, C₁–C₄-haloalkylthio having in    each case 1 to 9 fluorine, chlorine and/or bromine atoms,-   n represents 3, 4 or 5 and-   R⁵ represents identical or different radicals from the group    consisting of fluorine, chlorine, bromine, C₁–C₆-alkyl,    C₁–C₆-alkoxy, C₁–C₆-alkylthio, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy,    C₁–C₄-haloalkylthio having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms.

Particular preference is given to oxathiinecarboxamides of the formula(I) in which

-   R¹ represents fluorine,-   m represents 0 or 1,-   R represents one of the groupings below,

-   R² represents chlorine, bromine, methyl, ethyl, n-propyl, i-propyl,    n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio,    ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl, difluoromethoxy, trifluoromethoxy,    trifluoromethylthio, difluorochloromethyl-thio,-   R² furthermore represents cyano,-   R³ and R⁴ independently of one another represent fluorine, chlorine,    bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,    s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio,    trichloromethyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl, difluoromethoxy, trifluoromethoxy,    trifluoromethylthio, difluorochloromethylthio,-   n represents 3 or 4 and-   R⁵ represents identical or different radicals from the group    consisting of fluorine, chlorine, bromine, methyl, ethyl, n-propyl,    i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy,    methylthio, ethylthio, trichloromethyl, trifluoromethyl,    difluoromethyl, difluorochloromethyl, difluoromethoxy,    trifluoromethoxy, trifluoromethylthio, difluorochloromethylthio

Very particular preference is given to oxathiinecarboxamides of theformula (I), in which

-   R¹ represents fluorine,-   m represents 0 or 1,-   R represents one of the groupings below,

-   R² represents chlorine, bromine, methyl, ethyl, n-propyl, i-propyl,    n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio,    ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl,    trifluoromethoxy, trifluoromethylthio,-   R² furthermore represents cyano,-   R³ and R⁴ independently of one another represent fluorine, chlorine,    bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,    s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio,    trichloromethyl, trifluoromethyl, difluoromethyl, trifluoromethoxy,    trifluoromethylthio,-   n represents 3 and-   R⁵ represents identical or different radicals from the group    consisting of fluorine, chlorine, bromine, methyl, ethyl, n-propyl,    i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy,    methylthio, ethylthio, trichloromethyl, trifluoromethyl,    difluoromethyl, trifluoromethoxy, trifluoromethylthio.

Especially preferred are oxathiinecarboxamides of the formula (I), inwhich

-   R¹ represents fluorine,-   m represents 0 or 1,-   R represents one of the groupings below,

-   R² represents chlorine, bromine, t-butyl, methoxy, methylthio,    trichloromethyl, trifluoromethyl, trifluoromethoxy,    trifluoromethylthio,-   R² furthermore represents cyano,-   R³ and R⁴ independently of one another represent fluorine, chlorine,    methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy,    trifluoromethylthio,-   R⁵ represents identical or different radicals from the group    consisting of fluorine, chlorine, methyl, methoxy, methylthio,    trifluoromethyl, trifluoromethoxy, trifluoromethylthio

Emphasis is furthermore given to compounds of the formula (I) in which mrepresents 0.

Emphasis is furthermore given to compounds of the formula (I) in which Rrepresents the grouping

and R² as the general, preferred, particularly preferred, veryparticularly preferred and/or especially preferred meanings given above.

Emphasis is furthermore given to compounds of the formula (I) in which Rrepresents one of the groupings below

and R³ and R⁴ have the general, preferred, particularly preferred, veryparticularly preferred and/or especially preferred meanings given above.

Emphasis is furthermore given to compounds of the formula (I) in whichR³ and R⁴ independently of one another represent fluorine, chlorine orbromine.

Emphasis is furthermore given to compounds of the formula (I-a)

in which

-   R¹ represents fluorine,-   m represents 0 or 1,-   R² represents chlorine, bromine, methyl, ethyl, n-propyl, i-propyl,    n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio,    ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl, difluoromethoxy, trifluoromethoxy,    trifluoromethylthio, difluorochloromethylthio,-   R² furthermore represents cyano.

Emphasis is furthermore given to compounds of the formula (I-b)

in which

-   R¹ represents fluorine,-   m represents 0 or 1,-   R³ and R⁴ independently of one another represent fluorine, chlorine,    bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,    s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio,    trichloromethyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl, difluoromethoxy, trifluoromethoxy,    trifluoromethylthio, difluorochloromethylthio.

Emphasis is furthermore given to compounds of the formula (I-c)

in which

-   R¹ represents fluorine,-   m represents 0 or 1,-   R³ and R⁴ independently of one another represent fluorine, chlorine,    bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,    s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio,    trichloromethyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl, difluoromethoxy, trifluoromethoxy,    trifluoromethylthio, difluorochloromethylthio.

Emphasis is furthermore given to compounds of the formula (I-d)

in which

-   R¹ represents fluorine,-   m represents 0 or 1,-   R³ and R⁴ independently of one another represent fluorine, chlorine,    bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,    s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio,    trichloromethyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl, difluoromethoxy, trifluoromethoxy,    trifluoromethylthio, difluorochloromethylthio.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched as far as this ispossible, including in combination with heteroatoms, such as, forexample, in alkoxy.

Optionally substituted radicals can be mono- or polysubstituted, wherein the case of polysubstitution the substituents can be identical ordifferent.

Halogen-substituted radicals, such as, for example, haloalkyl, are mono-or polyhalogenated. In the case of polyhalogenation, the halogen atomscan be identical or different. Here, halogen represents fluorine,chlorine, bromine and iodine, in particular fluorine, chlorine andbromine.

However, the general or preferred radical definitions or illustrationsgiven above can also be combined with one another as desired, i.e.including combinations between the respective ranges and preferredranges. The definitions apply both to the end products and to theprecursors and intermediates. Moreover, individual definitions may notapply.

Using 2-methyl-5,6-dihydro-1,4-oxathiine-3-carbonylchloride and4′-chloro-2′-fluoro-1,1′-biphenyl-2-amine as starting materials, thecourse of the process (a) according to the invention can be illustratedby the formula scheme below.

Using N-(2-bromophenyl)-2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxamideand 4-chloro-2-fluorophenylboronic acid as starting materials and acatalyst, the course of the process (b) according to the invention canbe illustrated by the formula scheme below.

Using2-{[(2-methyl-5,6-dihydro-1,4-oxathiin-3-yl)carbonyl]amino}phenylboronicacid and 1-bromo-4-chloro-2-fluorobenzene as starting materials and acatalyst, the course of the process (c) according to the invention canbe illustrated by the formula scheme below.

Using N-(2-bromophenyl)-2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxamideand 1-bromo-4-chloro-2-fluorobenzene as starting materials and acatalyst and4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, the courseof the process (d) according to the invention can be illustrated by theformula scheme below.

Explanation of the Processes and Intermediates

The formula (II) provides a general definition of the carboxylic acidderivatives required as starting materials for carrying out the process(a) according to the invention. In this formula, G preferably representschlorine, bromine, hydroxyl, methoxy or ethoxy, particularly preferablychlorine, hydroxyl or methoxy, very particularly preferably chlorine.

The carboxylic acid derivative of the formula (II) are known or can beprepared by known processes (cf. EP-A 0 545 099 and EP-A 0 589 313).

The formula (III) provides a general definition of the analinederivatives required as reaction components for carrying out the process(a) according to the invention. In this formula, R, R¹ and m preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred, very particularlypreferred or especially preferred for these radicals or these indices.

The aniline derivatives of the formula (III) are known and/or some ofthem can be prepared by known methods (cf. EP-A 0 545 099 and EP-A 0 589301). Aniline derivatives of the formula (III) are obtained, forexample, by

-   e) reacting 2-haloaniline derivatives of the general formula (VIII)

-   -   in which    -   R¹ and m are as defined above and    -   Hal represents halogen,    -   with boronic acid derivatives of the formula (V)

-   -   in which    -   R is as defined above, and    -   if appropriate in the presence of an acid binder, if appropriate        in the presence of an inert organic diluent and if appropriate        in the presence of a catalyst, or

-   f) reacting anilineboronic acids of the formula (IX)

-   -   in which    -   R¹, m, G¹ and G² are as defined above    -   with phenyl derivatives of the formula (VII)

-   -   in which    -   R is as defined above,    -   if appropriate in the presence of an acid binder, if appropriate        in the presence of an inert organic diluent and if appropriate        in the presence of a catalyst.

The formula (VIII) provides a general definition of the two-haloanilinederivatives required as reaction components for carrying out the process(e) according to the invention. In this formula, R¹ and m preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred, very particularlypreferred or especially preferred for these radicals or indices. Halpreferably represents fluorine, chlorine or bromine, particularlypreferably chlorine or bromine.

The 2-haloaniline derivatives of the formula (VIII) are known and/or canbe prepared from the corresponding nitro compounds by reduction.

The boronic acid derivatives of the formula (V) furthermore required asstarting materials for carrying out the process (e) according to theinvention are explained in more detail below, in connection with theprocess (b) according to the invention.

Formula (IX) provides a general definition of the anilineboronic acidsrequired as reaction components for carrying out the process (f)according to the invention. In this formula, R¹ and m preferably havethose meanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred, very particularlypreferred or especially preferred for these radicals or these indices.G¹ and G² preferably each represent hydrogen or together representtetramethylethylene.

The anilineboronic acids of the formula (IX) are known and/or can beobtained by known methods.

The phenyl derivatives of the formula (VII) furthermore required asstarting materials for carrying out the process (f) according to theinvention are explained in more detail below, in connection with theprocess (d) according to the invention.

The formula (IV) provides a general definition of the carboxamidederivatives required as starting materials for carrying out theprocesses (b) and (d) according to the invention. In this formula, R¹and m preferably have those meanings which have already been mentionedin connection with the description of the compounds of the formula (I)according to the invention as being preferred, particularly preferred,very particularly preferred or especially preferred for these radicalsor these indices.

The carboxamide derivatives of the formula (IV) are known or can beprepared by known processes (for example from a carboxylic acidderivative of the formula (III) and a 2-bromoaniline derivative).

The formula (V) provides a general definition of the boronic acidderivatives required as starting materials for carrying out theprocesses (b) and (e) according to the invention. In this formula, Rpreferably has those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred, particularly preferred,very particularly preferred and especially preferred for this radical.G¹ and G² preferably each represent hydrogen or together representtetramethylethylene.

The boronic acid derivatives of the formula (V) are known and/or can beprepared by known processes (cf., for example, WO 01/90084 and U.S. Pat.No. 5,633,218).

They are obtained, for example, by

g) reacting phenyl derivatives of the formula (VII)

-   -   in which    -   R is as defined above,    -   with boric acid esters of the formula (X)        B(OR⁶)₃  (X)    -   in which    -   R⁶ represents C₁–C₄-alkyl,    -   in the presence of magnesium, if appropriate in the presence of        a diluent (for example tetrahydrofuran).

The formula (X) provides a general definition of the boric acid estersrequired as reaction components for carrying out the process (g)according to the invention. In this formula, R⁶ preferably representsmethyl, ethyl, n- or i-propyl, particularly preferably methyl or ethyl.

The boric acid esters of the formula (X) are known chemicals forsynthesis.

The formula (VI) provides a general definition of the carboximideboronic acid derivatives required as reaction components for carryingout the process (c) according to the invention. In this formula, R¹ andm preferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred, particularly preferred,very particularly preferred or especially preferred for these radicalsor these indices. G¹ and G² preferably each represent hydrogen ortogether represent tetramethylethylene.

The carboxamide boronic acid derivatives of the formula (VI) are knownand/or can be prepared by known processes.

The formula (VII) provides a general definition of the phenylderivatives required as starting materials for carrying out theprocesses (c), (d), (f) and (g) according to the invention. In thisformula, R preferably has those meanings which have already beenmentioned in connection with the description of the compounds of theformula (I) according to the invention as being preferred, particularlypreferred, very particularly preferred or especially preferred for thisradical.

The phenyl derivatives of the formula (VII) are known or can be preparedby known processes (cf. Synth. Commun. 2000, 30, 665–669, Synth. Commun.1999, 29, 1697–1701).

Suitable acid binders for carrying out the processes (a), (b), (c), (d),(e) and (f) according to the invention are in each case all inorganicand organic bases customary for such reactions. Preference is given tousing alkaline earth metal or alkali metal hydroxides, such as sodiumhydroxide, calcium hydroxide, potassium hydroxide, or else ammoniumhydroxide, alkali metal carbonates, such as sodium carbonate, potassiumcarbonate or potassium bicarbonate, sodium bicarbonate, alkali metal oralkaline earth metal acetates, such as sodium acetate, potassiumacetate, calcium acetate, and also tertiary amines, such astrimethylamine, triethylamine, tributylamine, N,N-dimethylaniline,pyridine, N-methylpiperidine, N,N-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiazabicycloundecene (DBU). However, it is also possible to work withoutthe addition of an acid binder, or to employ an excess of the aminecomponent so that it simultaneously acts as acid binder.

Suitable diluents for carrying out the processes (a), (b), (c), (d), (e)and (f) according to the invention are in each case all customary inertorganic solvents. Preference is given to using optionally halogenatedaliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether,hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene,xylene or decaline; chlorobenzene, dichlorobenzene, dichloromethane,chloroform, carbon tetrachloride, dichloroethane or trichloroethane;ethers, such as diethyl ether, diisopropyl ether, methyl-t-butyl ether,methyl-t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane or anisol; nitriles, such as acetonitrile,propionitrile, n- or i-butyronitrile or benzonitrile; amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide, esters, such asmethyl acetate or ethyl acetate; sulfoxides, such as dimethyl sulfoxide,or sulfones, such as sulfolane.

When carrying out the processes (a), (b), (c), (d), (e) and (f)according to the invention, the reaction temperatures can in each casebe varied within a relatively wide range. In general, the processes arecarried out at temperatures between 0° C. and 140° C., preferablybetween 10° C. and 120° C.

The processes (a), (b), (c), (d), (e) and (f) according to the inventionare generally each carried out under atmospheric pressure. However, ineach case it is also possible to operate under elevated or reducedpressure.

When carrying out the process (a) according to the invention, in general1 mol or else an excess of aniline derivative of the formula (III) andfrom 1 to 3 mol of acid binder are employed per mole of carboxylic acidderivative of the formula (II). However, it is also possible to employthe reaction components in other ratios. Work-up is carried out bycustomary methods. In general, water is added to the reaction mixtureand the organic phase is separated off and, after drying, concentratedunder reduced pressure. The residue that remains may, if appropriate, befreed of any impurities that may still be present using customarymethods, such as chromatography or recrystallization.

When carrying out the process (b) according to the invention, in general1 mol or else an excess of boronic acid derivative of the formula (V)and from 1 to 5 mol of acid binder are employed per mole of carboxamidederivative of the formula (IV). However, it is also possible to employthe reaction components in other ratios. Work-up is carried out bycustomary methods. In general, water is added to the reaction mixtureand the precipitate is separated off and dried. The reside that remainsmay, if appropriate, be freed of any impurities that may still bepresent using customary methods, such as chromatography orrecrystallization.

When carrying out the process (c) according to the invention, in general1 mol or else an excess of phenyl derivative of the formula (VII) andfrom 1 to 10 mol of acid binder and from 0.5 to 5 mol % of a catalystare employed per mole of carboxamide boronic acid derivative of theformula (VI). However, it is also possible to employ the reactioncomponents in other ratios. Work-up is carried out by customary methods.In general, water is added to the reaction mixture and the precipitateis separated off and dried. The residue that remains may, ifappropriate, be freed of any impurities that may still be present usingcustomary methods, such as chromatography or recrystallization.

When carrying out the process (d) according to the invention, in general1 mol or else an excess of phenyl derivative of the formula (VII) andfrom 1 to 5 mol of acid binder and from 1 to 5 mol of a catalyst areemployed per mole of carboxamide derivative of the formula (IV).However, it is also possible to employ the reaction components in otherratios. Work-up is carried out by customary methods. In general, wateris added to the reaction mixture and the precipitate is separated offand dried. The residue that remains may, if appropriate, be freed of anyimpurities that may still be present using customary methods, such aschromatography or recrystallization.

The substances according to the invention have potent microbicidalactivity and can be employed for controlling unwanted micro-organisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

-   Xanthomonas species, such as, for example, Xanthomonas campestris    pv. oryzae;-   Pseudomonas species, such as, for example, Pseudomonas syringae pv.    lachrymans;-   Erwinia species, such as, for example, Erwinia amylovora;-   Pythium species, such as, for example, Pythium ultimum;-   Phytophthora species, such as, for example, Phytophthora infestans;-   Pseudoperonospora species, such as, for example, Pseudoperonospora    humuli or Pseudoperonospora cubensis;-   Plasmopara species, such as, for example, Plasmopara viticola;-   Bremia species, such as, for example, Bremia lactucae;-   Peronospora species, such as, for example, Peronospora pisi or P.    brassicae;-   Erysiphe species, such as, for example, Erysiphe graminis;-   Sphaerotheca species, such as, for example, Sphaerotheca graminis;-   Podosphaera species, such as, for example, Podosphaera leucotricha;-   Venturia species, such as, for example, Venturia inaequalis;-   Pyrenophora species, such as, for example, Pyrenophora teres or P.    graminea (conidia form: Drechslera, syn: Helminthosporium);-   Cochliobolus species, such as, for example, Cochliobolus sativus    (conidia form: Drechslera, syn: Helminthosporium);-   Uromyces species, such as, for example, Uromyces appendiculatus;-   Puccinia species, such as, for example, Puccinia recondita;-   Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;-   Tilletia species, such as, for example, Tilletia caries;-   Ustilago species, such as, for example, Ustilago nuda or Ustilago    avenae;-   Pellicularia species, such as, for example, Pellicularia sasakii;-   Pyricularia species, such as, for example, Pyricularia oryzae;-   Fusarium species, such as, for example, Fusarium culmorum;-   Botrytis species, such as, for example, Botrytis cinerea;-   Septoria species, such as, for example, Septoria nodorum;-   Leptosphaeria species, such as, for example, Leptosphaeria nodorum;-   Cercospora species, such as, for example, Cercospora canescens;-   Alternaria species, such as, for example, Alternaria brassicae; and-   Pseudocercosporella species, such as, for example,    Pseudocercosporella herpotrichoides.

The active compounds according to the invention also have very goodfortifying action in plants. Accordingly, they can be used formobilizing the defences of the plant against attack by unwantedmicro-organisms.

In the present context, plant-fortifying (resistance-inducing)substances are to be understood as meaning those substances which arecapable of stimulating the defence system of plants such that, when thetreated plants are subsequently inoculated with unwantedmicro-organisms, they show substantial resistance against thesemicro-organisms.

In the present case, unwanted micro-organisms are to be understood asmeaning phytopathogenic fungi, bacteria and viruses. Accordingly, thesubstances according to the invention can be used to protect plants fora certain period after the treatment against attack by the pathogensmentioned. The period for which protection is provided generally extendsover 1 to 10 days, preferably 1 to 7 days, after the treatment of theplants with the active compounds.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The active compounds according to the invention are also suitable forincreasing the yield of crops. In addition, they show reduced toxicityand are well tolerated by plants.

At certain concentrations and application rates, the active compoundsaccording to the invention can also be used as herbicides, forinfluencing plant growth and for controlling animal pests. They can alsobe used as intermediates and precursors for the synthesis of furtheractive compounds.

The active compounds according to the invention can be used to treat allplants and parts of plants. By plants are understood here all plants andplant populations such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding the plant varieties which can or cannot be protected byvarietal property rights. Parts of plants are to be understood asmeaning all above-ground and below-ground parts and organs of plants,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stems, trunks, flowers, fruit-bodies, fruits andseeds and also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and the parts of plants with the activecompounds according to the invention is carried out directly or byaction on their surroundings, habitat or storage space, according tocustomary treatment methods, for example by dipping, spraying,evaporating, atomizing, broadcasting, spreading-on and, in the case ofpropagation material, in particular in the case of seeds, furthermore byone- or multi-layer coating.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, undesired micro-organisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be adhesives, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, micro-organisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of micro-organisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably adhesives, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Micro-organisms capable of degrading or changing the industrialmaterials which may be mentioned are, for example, bacteria, fungi,yeasts, algae and slime organisms. The active compounds according to theinvention preferably act against fingi, in particular moulds,wood-discolouring and wood-destroying fungi (Basidiomycetes), andagainst slime organisms and algae.

Micro-organisms of the following genera may be mentioned as examples:

-   Alternaria, such as Alternaria tenuis,-   Aspergillus, such as Aspergillus niger,-   Chaetomium, such as Chaetomium globosum,-   Coniophora, such as Coniophora puetana,-   Lentinus, such as Lentinus tigrinus,-   Penicillium, such as Penicillium glaucum,-   Polyporus, such as Polyporus versicolor,-   Aureobasidium, such as Aureobasidium pullulans,-   Sclerophoma, such as Sclerophoma pityophila,-   Trichoderma, such as Trichoderma viride,-   Escherichia, such as Escherichia coli,-   Pseudomonas, such as Pseudomonas aeruginosa, and-   Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Essentially,suitable liquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates, or else proteinhydrolysates. Suitable dispersants are: for example lignosulphite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such orin their formulations, also in a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum or to prevent development of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Examples of suitable mixing components are the following:

Fungicides:

-   aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,    azaconazole, azoxystrobin,-   benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,    bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,    bromuconazole, bupirimate, buthiobate,-   calcium polysulphide, carpropamide, capsimycin, captafol, captan,    carbendazim, carboxin, carvon, quinomethionate, chlobenthiazone,    chlorfenazole, chloroneb, chloropicrin, chlorothalonil,    chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole,    cyprodinil, cyprofuram,-   debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,    dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,    diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,    ditalimfos, dithianon, dodemorph, dodine, drazoxolon,-   edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,-   famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram,    fenhexamide, fenitropan, fenpiclonil, fenpropidin, fenpropimorph,    fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam,    flumetover, fluoromide, fluquinconazole, flurprimidol, flusilazole,    flusulphamide, flutolanil, flutriafol, folpet, fosetyl-aluminium,    fosetyl-sodium, fthalide, fuberidazole, furalaxyl, furametpyr,    furcarbonil, furconazole, furconazole-cis, furmecyclox,-   guazatine, hexachlorobenzene, hexaconazole, hymexazole,-   imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,    iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),    iprodione, iprovalicarb, irumamycin, isoprothiolane, isovaledione,-   kasugamycin, kresoxim-methyl, copper preparations, such as: copper    hydroxide, copper naphthenate, copper oxychloride, copper sulphate,    copper oxide, oxine-copper and Bordeaux mixture,-   mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,    metalaxyl, metconazole, methasulphocarb, methfuroxam, metiram,    metomeclam, metsulphovax, mildiomycin, myclobutanil, myclozolin,-   nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,-   ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim,    oxyfenthiin,-   paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,    picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim,    probenazole, prochloraz, procymidone, propamocarb,    propanosine-sodium, propiconazole, propineb, pyraclostrobin,    pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,-   quinconazole, quintozene (PCNB), quinoxyfen,-   sulphur and sulphur preparations, spiroxamines,-   tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,    thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,    tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,    triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,    trifloxystrobin, triflumizole, triforine, triticonazole,-   uniconazole,-   validamycin A, vinclozolin, viniconazole,-   zarilamide, zineb, ziram and also-   Dagger G, OK-8705, OK-8801,-   α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,-   α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,-   (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,-   (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,-   1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone    O-(phenylmethyl)-oxime,-   1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,-   1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,-   1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,-   1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,-   1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,-   1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,-   1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,-   2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,-   2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,-   2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,-   2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,-   2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,-   2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,-   2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,-   2-aminobutane,-   2-bromo-2-(bromomethyl)-pentanedinitrile,-   2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,-   2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,-   2-phenylphenol (OPP),-   3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,-   3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,-   3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,-   3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,-   4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,-   4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,-   8-hydroxyquinoline sulphate,-   9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,-   bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,-   cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,-   cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine-hydrochloride,-   ethyl [(4-chlorophenyl)-azo]-cyanoacetate,-   potassium hydrogen carbonate,-   methanetetrathiol sodium salt,-   methyl    1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,-   methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,-   methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,-   N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,-   N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,-   N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,-   N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,-   N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,-   N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,-   N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,-   N-formyl-N-hydroxy-DL-alanine-sodium salt,-   O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,-   O-methyl S-phenyl phenylpropylphosphoramidothioate,-   S-methyl 1,2,3-benzothiadiazole-7-carbothioate,-   spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,-   4-[(3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-acryloyl]-morpholine.    Bactericides:-   bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,    kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,    probenazole, streptomycin, tecloftalam, copper sulphate and other    copper preparations.    Insecticides/Acaricides/Nematicides:-   abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,    aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin,    AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphos M,    azocyclotin,-   Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus    thuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,    bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,    bifenazate, bifenthrin, bioethanomethrin, biopermethrin,    bistrifluron, BPMC, bromophos A, bufencarb, buprofezin, butathiofos,    butocarboxim, butylpyridaben,-   cadusafos, carbaryl, carbofuran, carbophenothion, carbosulphan,    cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,    chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,    chlovaporthrin, chromafenozide, cisresmethrin, cispermethrin,    clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,    cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,    cypermethrin, cyromazine,-   deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,    diazinon, dichlorvos, dicofol, diflubenzuron, dimethoat,    dimethylvinphos, diofenolan, disulphoton, docusat-sodium, dofenapyn,-   eflusilanate, emamectin, empenthrin, endosulphan, Entomopfthora    spp., esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,    etoxazole, etrimfos,-   fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,    fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,    fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazuron,    flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,    flumethrin, flutenzine, fluvalinate, fonophos, fosmethilan,    fosthiazate, ftubfenprox, furathiocarb,-   granulosis viruses,-   halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,    hydroprene,-   imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion,    ivermectin,-   nuclear polyhedrosis viruses,-   lambda-cyhalothrin, lufenuron,-   malathion, mecarbam, metaldehyde, methamidophos, Metharhizium    anisopliae, Metharhizium flavoviride, methidathion, methiocarb,    methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone,    mevinphos, milbemectin, milbemycin, monocrotophos,-   naled, nitenpyram, nithiazine, novaluron,-   omethoate, oxamyl, oxydemethon M,-   Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,    phenthoate, phorat, phosalone, phosmet, phosphamidon, phoxim,    pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,    propargite, propoxur, prothiofos, prothoat, pymetrozine, pyraclofos,    pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen,    pyriproxyfen,-   quinalphos, ribavirin,-   salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulphotep,    sulprofos,-   tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,    teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,    tetrachlorvinphos, tetradifon theta-cypermethrin, thiacloprid,    thiamethoxarn, thiapronil, thiatriphos, thiocyclam hydrogen oxalate,    thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,    triarathene, triazamate, triazophos, triazuron, trichlophenidine,    trichlorfon, triflumuron, trimethacarb,-   vamidothion, vaniliprole, Verticillium lecanii,-   YI 5302, Zeta-cypermethrin, Zolaprofos-   (1R-cis)-[5-(phenylmethyl)-3-franyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,-   (3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,-   1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,-   2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,-   2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,-   2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,-   2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,-   3-methylphenyl propylcarbamate-   4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,-   4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,-   4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,-   4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,-   Bacillus thuringiensis strain EG-2348,-   [2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,-   2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl    butanoate,-   [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,-   dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,-   ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,-   N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,-   N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,-   N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,-   N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,-   N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,-   O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,-   N-cyanomethyl-4-trifluoromethyl-nicotinamide,-   3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridine-2-yloxy)-propoxy]-benzene.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, is also possible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi, (for example against Candida species,such as Candida albicans, Candida glabrata), and Epidermophytonfloccosum, Aspergillus species, such as Aspergillus niger andAspergillus fumigatus, Trichophyton species, such as Trichophytonmentagrophytes, Microsporon species such as Microsporon canis andaudouinii. The list of these fungi by no means limits the mycoticspectrum covered, but is only for illustration.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is furthermore possible to apply the activecompounds by the ultra-low volume method, or to inject the activecompound preparation or the active compound itself into the soil. It isalso possible to treat the seeds of the plants.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. For the treatment of partsof plants, the active compound application rates are generally between0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. For seeddressing, the active compound application rates are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For the treatment of the soil, the active compoundapplication rates are generally between 0.1 and 10,000 g/ha, preferablybetween 1 and 5000 g/ha.

As already mentioned above, it is possible to treat all plants and theirparts with active compounds according to the invention. In a preferredembodiment, wild plant species and plant cultivars, or those obtained byconventional biological breeding, such as crossing or protoplast fusion,and parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetical engineering,if appropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnew properties (“traits”) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can becultivars, varieties, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possiblewhich exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably treated according to the inventioninclude all plants which, in the genetic modification, received geneticmaterial which imparted particularly advantageous useful properties(“traits”) to these plants. Examples of such properties are better plantgrowth, increased tolerance to high or low temperatures, increasedtolerance to drought or to water or soil salt content, increasedflowering performance, easier harvesting, accelerated maturation, higherharvest yields, better quality and/or a higher nutritional value of theharvested products, better storage stability and/or processability ofthe harvested products. Further and particularly emphasized examples ofsuch properties are a better defence of the plants against animal andmicrobial pests, such as against insects, mites, phytopathogenic fungi,bacteria and/or viruses, and also increased tolerance of the plants tocertain herbicidally active compounds. Examples of transgenic plantswhich may be mentioned are the important crop plants, such as cereals(wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape andalso fruit plants (with the fruits apples, pears, citrus fruits andgrapes), and particular emphasis is given to maize, soya beans,potatoes, cotton and oilseed rape. Traits that are emphasized are inparticular increased defence of the plants against insects by toxinsformed in the plants, in particular those formed in the plants by thegenetic material from Bacillus thuringiensis (for example by the genesCryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab,Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred toas “Bt plants”). Traits that are also particularly emphasized are theincreased defence of the plants to fungi, bacteria and viruses bysystemic acquired resistance (SAR), systemin, phytoalexins, elicitorsand resistance genes and correspondingly expressed proteins and toxins.Traits that are furthermore particularly emphasized are the increasedtolerance of the plants to certain herbicidally active compounds, forexample imidazolinones, sulphonylureas, glyphosate or phosphinotricin(for example the “PAT” gene). The genes which impart the desired traitsin question can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylurea, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example maize). Of course, thesestatements also apply to plant cultivars having these genetic traits orgenetic traits still to be developed, which plants will be developedand/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the formula (I)according to the invention or the active compound mixtures according tothe invention. The preferred ranges stated above for the activecompounds or mixtures also apply to the treatment of these plants.Particular emphasis is given to the treatment of plants with thecompounds and mixtures specifically mentioned in the present text.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1

332 mg of 4′-chloro-2′-fluoro-1,1′-biphenyl-2-amine and 268 mg of2-methyl-5,6-dihydro-1,4-oxathiine-3-carbonyl chloride are addeddropwise to a suspension of 207 mg of potassium carbonate in 25 ml ofacetonitrile. The reaction mixture is stirred for 10 h. For work-up, 20ml of water are added to the reaction solution and the mixture isextracted with ethyl acetate. The organic phases are dried with sodiumsulphate and concentrated. The residue is chromatographed on silica gel(cyclohexane/ethyl acetate 2:1).

This gives 220 mg (39%) ofN-(4′-chloro-2′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxamideof logP (pH 2.3)=3.61.

The oxathiinecarboxamides of the formula (I) listed in Table 1 below arelikewise prepared analogously to Example 1 described above and inaccordance with the general descriptions of the processes.

TABLE 1 (I)

Ex. M R¹ R logP (pH 2.3)/m.p. 2 0 —

3.97 3 0 —

4.21 4 0 —

3.83 5 0 —

3.89 6 0 —

4.0297° C. 7 0 —

8 0 —

4.26 9 0 —

3.67 10 0 —

3.70 11 0 —

4.22 12 0 —

3.38 13 0 —

4.03 14 1 4-F

4.00 15 0 —

4.17 16 1 2-F

3.53 17 0 —

3.69 18 0 —

3.24 19 0 —

2.74 20 0 —

3.76117–119° C. 21 0 —

3.80 22 0 —

23 0 —

3.56 24 0 —

3.38oil 25 0 —

4.02103–105° C.

The logP values given in the Preparation Examples were determined inaccordance with EEC Directive 79/831 Annex V.A8 by HPLC (HighPerformance Liquid Chromatography) using a reversed-phase column (C 18).Temperature: 43° C.

Mobile phases for the determination in the acidic range: 0.1% aqueousphosphoric acid, acetonitrile; linear gradients from 10% acetonitrile to90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (having 3 to16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones).

The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 m to 400 nm.

USE EXAMPLES Example A

Podosphaera Test (Apple)/Protective

-   Solvents: 24.5 Parts by weight of acetone 24.5 Parts by weight of    dimethylacetamide-   Emulsifier: 1.0 Part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of the apple mildew pathogen Podosphaera leucotricha.The plants are then placed in a greenhouse at about 23° C. and arelative atmospheric humidity of about 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE A Podosphaera Test (Apple)/protective Active compound applicationEfficacy Active compound rate in g/ha in % 6

100 100 9

100 100 10

100 93 15

100 98 16

100 90 7

100 100 8

100 96 1

100 99

Example B

Venturia Test (Apple)/protective Solvents: 24.5 Parts by weight ofacetone 24.5 Parts by weight of dimethylacetamide Emulsifier: 1.0 Partby weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the apple scab pathogen Venturia inaequalis andthen remain in an incubation cabin at about 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE B Venturia Test (Apple)/protective Active compound Efficacy Activecompound in g/ha in % 6

100 100 9

100 100 10

100 100 15

100 100 16

100 100 17

100 93 7

100 100 8

100 99 12

100 100 13

100 99 1

100 100

Example C

Alternaria Test (Tomato)/protective Solvent: 49 Parts by weight ofN,N-dimethylformamide Emulsifier: 1 part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young tomato plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with an aqueous sporesuspension of Alternaria solani. The plants are then placed in anincubation cabin at about 20° C. and 100% relative atmospheric humidity.

Evaluation is carried out 2 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE C Alternaria Test (Tomato)/protective Active compound EfficacyActive compound in g/ha in % 6

100 100 9

100 100 10

100 94 15

100 96 16

100 95 17

100 93 7

100 98 8

100 94 12

100 95 13

100 94 1

100 94

Example D

Pyrenophora teres Test (Barley)/protective Solvent: 25 Parts by weightof N,N-dimethylacetamide Emulsifier: 0.6 Part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Pyrenophora teres. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at temperature of about 20°C. and a relative atmospheric humidity of about 80%.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE D Pyrenophora teres - Test (Barley)/protective Active compoundEfficacy Active compound in g/ha in % 9

500 95 17

500 100 19

500 93

Example E

Puccinia Test (Wheat)/protective Solvent: 25 parts by weight ofN,N-dimethylacetamide Emulsifier: 0.6 part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Puccinia recondita. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of about 80% to promote thedevelopment of rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE E Puccinia Test (Wheat)/protective Active compound Efficacy Activecompound in g/ha in % 9

500 100 6

500 100

1. An oxathiinecarboxamide of formula (I)

in which R¹ represents fluorine, m represents 0, 1, or 2, R representsone of the groups

R² represents chlorine, bromine, iodine, cyano, nitro, C₁–C₈-alkyl,C₁–C₈-alkoxy, C₁–C₈-alkylthio, C₁–C₆-haloalkyl, C₁–C₆-haloalkoxy, orC₁–C₆-haloalkylthio, each halo-containing group having from 1 to 13fluorine, chlorine, and/or bromine atoms, R³ and R⁴ independently of oneanother represent fluorine, chlorine, bromine, iodine, cyano, nitro,C₁–C₈-alkyl, C₁–C₈-alkoxy, C₁–C₈-alkylthio, C₁–C₆-haloalkyl,C₁–C₆-haloalkoxy, or C₁–C₆-haloalkylthio, each halo-containing grouphaving 1 to 13 fluorine, chlorine, and/or bromine atoms, n represents 3,4, or 5, and R⁵ represents identical or different radicals selected fromthe group consisting of fluorine, chlorine, bromine, iodine, cyano,nitro, C₁–C₈-alkyl, C₁–C₈-alkoxy, C₁–C₈-alkylthio, C₁–C₆-haloalkyl,C₁–C₆-haloalkoxy, and C₁–C₆-haloalkylthio, each halo-containing grouphaving 1 to 13 fluorine, chlorine, and/or bromine atoms.
 2. Anoxathiinecarboxamide of formula (I) according to claim 1 in which R¹represents fluorine, m represents 0, 1, or 2, R represents one of thegroups

R² represents chlorine, bromine, cyano, C₁–C₆-alkyl, C₁–C₆-alkoxy,C₁–C₆-alkylthio, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, orC₁–C₄-haloalkylthio, each halo-containing group having 1 to 9 fluorine,chlorine, and/or bromine atoms, R³ and R⁴ independently of one anotherrepresent fluorine, chlorine, bromine, C₁–C₆-alkyl, C₁–C₆-alkoxy,C₁–C₆-alkylthio, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, orC₁–C₄-haloalkylthio, each halo-containing group having 1 to 9 fluorine,chlorine, and/or bromine atoms, n represents 3, 4, or 5, and R⁵represents identical or different radicals selected from the groupconsisting of fluorine, chlorine, bromine, C₁–C₆-alkyl, C₁–C₆-alkoxy,C₁–C₆-alkylthio, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, andC₁–C₄-haloalkylthio, each halo-containing group having 1 to 9 fluorine,chlorine, and/or bromine atoms.
 3. An oxathiinecarboxamide of formula(I) according to claim 1 in which R¹ represents fluorine, m represents0or 1, R represents one of the groups

R² represents chlorine, bromine, cyano, methyl, ethyl, n-propyl,i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy,methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl, difluoromethoxy, trifluoromethoxy,trifluoromethylthio, or difluorochloromethylthio, R³ and R⁴independently of one another represent fluorine, chlorine, bromine,methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,methoxy, ethoxy, methylthio, ethylthio, trichloromethyl,trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy,trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio, nrepresents 3 or 4, and R⁵ represents identical or different radicalsselected from the group consisting of fluorine, chlorine, bromine,methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,methoxy, ethoxy, methylthio, ethylthio, trichloromethyl,trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy,trifluoromethoxy, trifluoromethylthio, and difluorochloromethylthio. 4.An oxathiinecarboxamide of formula (I) according to claim 1 in which R¹represents fluorine, m represents 0 or 1, R represents one of the groups

R² represents chlorine, bromine, cyano, methyl, ethyl, n-propyl,i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy,methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl,trifluoromethoxy, or trifluoromethylthio, R³ and R⁴ independently of oneanother represent fluorine, chlorine, bromine, methyl, ethyl, n-propyl,i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy,methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl,trifluoromethoxy, or trifluoromethylthio, n represents 3, and R⁵represents identical or different radicals selected from the groupconsisting of fluorine, chlorine, bromine, methyl, ethyl, n-propyl,i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy,methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl,trifluoromethoxy, and trifluoromethylthio.
 5. An oxathiinecarboxamide offormula (I) according to claim 1 in which R¹ represents fluorine, mrepresents 0 or 1, represents one of the groups

R² represents chlorine, bromine, cyano, t-butyl, methoxy, methylthio,trichloromethyl, trifluoromethyl, trifluoromethoxy, ortrifluoromethylthio, R³ and R⁴ independently of one another representfluorine, chlorine, methyl, methoxy, methylthio, trifluoromethyl,trifluoromethoxy, or trifluoromethylthio, and R⁵ represents identical ordifferent radicals selected from the group consisting of fluorine,chlorine, methyl, methoxy, methylthio, trifluoromethyl,trifluoromethoxy, and trifluoromethylthio.
 6. An oxathiinecarboxamideaccording to claim 1 of formula (I-a)

in which R¹ represents fluorine, m represents 0 or 1, and R² representschlorine, bromine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl,i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio,trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl,difluoromethoxy, trifluoromethoxy, trifluoromethylthio, ordifluorochloromethylthio.
 7. An oxathiinecarboxamide according to claim1 of formula (I-b)

in which R¹ represents fluorine, m represents 0 or 1, and R³ and R⁴independently of one another represent fluorine, chlorine, bromine,methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,methoxy, ethoxy, methylthio, ethylthio, trichloromethyl,trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy,trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio. 8.An oxathiinecarboxamide according to claim 1 of formula (I-c)

in which R¹ represents fluorine, m represents 0 or 1, and R³ and R⁴independently of one another represent fluorine, chlorine, bromine,methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,methoxy, ethoxy, methylthio, ethylthio, trichloromethyl,trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy,trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio. 9.An oxathiinecarboxamide according to claim 1 of formula (I-d)

in which R¹ represents fluorine, m represents 0 or 1, and R³ and R⁴independently of one another represent fluorine, chlorine, bromine,methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,methoxy, ethoxy, methylthio, ethylthio, trichloromethyl,trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy,trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio. 10.A process for preparing oxathiinecarboxamides of formula (I) accordingto claim 1 comprising (a) reacting a carboxylic acid derivative offormula (II)

in which G represents halogen, hydroxyl, or C₁–C₆-alkoxy, with ananiline derivative of formula (III)

in which R, R¹, and mare as defined for formula (I) in claim 1,optionally in the presence of a catalyst, optionally in the presence ofan acid binder, and optionally in the presence of a diluent, or (b)reacting a carboxamide derivative of formula (IV)

in which R¹ and mare as defined for formula (I) in claim 1, with aboronic acid derivative of formula (V)

in which R is as defined for formula (I) in claim 1, and G¹ and G² eachrepresent hydrogen or together represent tetramethylethylene, in thepresence of a catalyst, optionally in the presence of an acid binder,and optionally in the presence of a diluent, or (c) reacting acarboxamide boronic acid derivative of formula (VI)

in which R¹ and m are as defined for formula (I) in claim 1, and G¹ andG² each represent hydrogen or together represent tetramethylethylene,with a phenyl derivative of formula (VII)

in which R is as defined for formula (I) in claim 1, in the presence ofa catalyst, optionally in the presence of an acid binder, and optionallyin the presence of a diluent, or (d) reacting a carboxamide derivativeof formula (IV)

in which R¹ and m are as defined for formula (I) in claim 1, with aphenyl derivative of formula (VII)

in which R is as defined for formula (I) in claim 1, in the presence ofa palladium or platinum catalyst, in the presence of4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, optionallyin the presence of an acid binder, and optionally in the presence of adiluent.
 11. A composition for controlling unwanted micro-organismscomprising one or more oxathiinecarboxamides of formula (I) according toclaim 1 and one or more extenders and/or surfactants.
 12. A method forcontrolling unwanted micro-organisms comprising applying an effectiveamount of one or more oxathiinecarboxamide of formula (I) according toclaim 1 to the micro-organisms and/or their habitat.
 13. A process forpreparing compositions for controlling unwanted micro-organismscomprising mixing one or more oxathiinecarboxamides of formula (I)according to claim 1 with one or more extenders and/or surfactants.